Water-insoluble monoazo dyestuffs



2,849,438 7 WATER-INSOLUBLE MoNoAzo DYESTUFFS Gerd Muller, Koln-Flittard, Franz Bechlars and Herbert etzner, Leverkusen, and Hartmut Grahmann, Kolnassignors to Farbenfabriken Bayer Leverlrusen, Germany, a corporaermany No Drawing. Application June 27, 1955 Serial No. $594,097

Claims priority, application Germany July 20, 1955 Claims. (Cl. 260204) to the following formula:

- r z n (30.HNR CHqCOJIN N- N 2': N02 wherein R stands for a benzene radical which may be further substituted and X, Y and Z halogeno, alkyl, alk-oxy or nitro groups.

t is an object of the present invention to provide new mean hydrogen,

paints, called spinning process.

The following examples are given for the purpose of illustrating the invention, without, however, limiting it thereto; the parts being by weight.

Example 1 good fastness to light, to atmospheric good fastness to solvents. Th ifor dyeing plastic masses or spinning solutions and i printing.

and represents a brown 2,849,438 Patented Aug. 26, 1958 Example 2 39.5 parts of 1-(2',3-hydroxy-naphthoylamino)-2,4- dimethoxy-5-chlore-benzene are dissolved in dilute lye. Af

ture is heated to 40 C. f is completed. The washed and dried. formula:

22.9 parts of l -amino-2-nitro-4-acetylamino-S-chlorosolution of 20.4 parts of 1-(2,3-hydroxy-naphthoylamino) -2-methylbenzene in dilute soda lye. The mixture is heated to 40 coupling is complete. The resulting dyestufi is filtered powder which is distinguished by a very good solvent fastness.

lllf can be used to prepare a graphic printing;

it yields a red-brown print with very good light fastness. If, instead of 1-amino-2-nitro-4-acetylamino-S-chloroenzene, equivalent parts of l-amino-2-nitro-4-acetyl- 30.4 parts of l-(2,3'-hydroXy-naphthoyl amino)2-methylbenzene in dilute soda lye is introduced and The dyestulf thus with suction and dried. It corresponds to the following formula:

r-insoluble monoazo dyestufi corresponding no COflNQ azo dyestulf corresponding 7 4. The wate to the formula:

We claim: 1. A water-insoluble monoazo dyestufi corresponding to the following formula:

Y 2 HO CO.HN-B l 5 01110 O .HN- N=N l CH3 l X N02 wherein R is a member selected from the group consisting The water'msoluble mono of phenyl, halo-substituted phenyl', lower alkyl-substito the formula:

tuted phenyl, and lower-alkoxy X, Y and Z stand for a member selected from the group Y HO "O consisting of hydrogen, chlorine, lower alkyl, lower alkoxy E and nitro radicals.

2. The water-insoluble monoazo dyestufi corresponding to the formula: C1

1 10, no com: d in the file of this patent O UNITED STATES PATENTS CHaCOlIN N=N- CH3 2,025,117 Lubs et al. Dec. 24, 1935 2,218,920 Morschel et al. Oct. 22, 1940 OTHER REFERENCES hem. Soc. (London), 1928, pages 172-177.

References Cite 3. The water-insoluble monoazo dyestufi corresponding to the formula: lollmal C C1 Heflbron: Dlctionary of Organic Compounds 111, page HO CO.HN 0 CH:

l omcohN-O-Nm 00H, 

1. A WATER-INSOLUBLE MONOAZO DYESTUFF CORRESPONDING TO THE FOLLOWING FORMULA: 